Drew graduated from the University of Pennsylvania with a B.A. in Political Science in 2007. He moved to Washington, D.C. and worked as a political appointee at the U.S. Department of Homeland Security. Following this stint, he served in the U.S. Army as an Infantry Officer in the 82nd Airborne, deploying twice to Afghanistan. Drew left active duty to pursue his MBA at UNC Kenan-Flagler where he is focusing on a career in management consulting.